Cathie Black’s Emails Release: 5 Juiciest Bits

Mary Altaffer/AP

The Bloomberg administration reportedly spent more than $25,000 to fight the release of former publishing maven turned former New York City schools chancellor Cathie Black’s emails. Now it’s clear why: they’re pretty embarrassing.

The 78 pages of emails, released following a Freedom of Information Act request from Village Voice reporter Sergio Hernandez, reveal the obsessive stargazing strategy that was behind Black’s campaign to be appointed chancellor, despite, as chairman of Hearst Magazines, having no experience in the field of education. The Bloomberg administration defended its now-notorious struggle to keep the emails from being released by arguing that making them public might “discourage public discourse.” Also, perhaps, it’s because it reveals Black’s relentless, cringe-inducing pursuit of Oprah Winfrey.

From her hunt for big O to her desperate plea for Caroline Kennedy’s public endorsement, here are the juiciest bits of Black’s email dump.

1. The wooing of Oprah

The Black team’s aggressive efforts to land major celebrity endorsements, including a lofty plan to have high-profile women sign a letter of support, is on glaring display in the emails, particularly the pursuit of Oprah Winfrey. When Black finally landed her (with Gayle King’s help, natch), she still wanted to be in control of the message. So in case Winfrey—queen of all media/the universe, our souls, and best selves and angel of eloquence—was at a loss for words, Black, using third person to refer to herself, provided O with a script of things to say about her: “What a great schools chancellor. Tremendous leadership, excellent manager, innovator, mother of two and cares about the future of all children. Grace under pressure.” Of course, in her actual interview, Winfrey’s own spin on those words was expectedly improved and brilliant: “She will be a tremendous champion for the children of New York and will do it with grace.”

2. The Oprah celebration

The team couldn’t have been more pleased with its big O coup. After Saint Winfrey blessed Black with her endorsement, the Daily News made it one of its cover stories. “O BACKS CATHIE,” the headline read, splitting front-page real estate with Kate Middleton. “Talk-show queen gushes over Bloomy’s controversial pick.” One staffer sent Black a giddy email with the subject, “Oprah knocked crime off the cover of the Daily News,” and “Walking past a newsstand this afternoon, I was surprised to learn that we succeeded in have Oprah knock a crime story off the cover of the News today—at least in the edition that’s sold on the streets. Surprise!”

3. No Trumps allowed

Black’s team sent feelers to an exhaustive list of high-profile women to get them to publicly endorse her, including, but not limited to, Winfrey, Caroline Kennedy, Diane von Furstenberg, Gloria Steinem, Bette Midler, Whoopi Goldberg, and Nora Ephron. But there was a line, and that line was the Trumps. “Would we want Ivanka Trump? Think she would do,” Black says in one email. “I would skip,” replies the mayor’s aide.

4. The great Kennedy hunt

Black apparently really wanted Caroline Kennedy’s endorsement. Like little-kid-wishing-for-a-puppy-for-Christmas wanted her backing. Multiple emails chronicle breathless back-and-forths between the team looking for Kennedy’s contact information. Once it was finally obtained, Black sent her an email beginning, “Though we have met only briefly, I just wanted to reach out and say hello.” She goes on: “No doubt you have seen some if not all of my relentless press of late,” and asks her to sign a letter of support. The email was sent at 5:53 a.m. At 4:02 p.m. the same day, Black sent a staff member a panicked note saying, “I sent this at the crack of dawn but no response. Have you heard anything?”

5. The self-doubt

As aggressively as Black pushed the campaign to have bold-faced names publicly gush about her in order to gain her favor, she wasn’t always sure it was working—particularly as the press pilloried the celebrity focus of the strategy. “Is our strategy working?” she asked in one email. “Based on nyt this am do we have to another course? Or hold steady? I am ok, honestly. Just need verification! Nice quote from mulgrew. Should I call to thank?”